Biomass-Based Polyureas Derived from Rigid Furfurylamine and Isomannide

Polyureas are important commercial polymers that are widely used in construction, automobile industry, military field, and coatings. Biomass-based amines are attractive feedstock in the synthesis of versatile polyureas. Furan-based diamine and isomannide-derived (Im-derived) diamine can be interesting monomers for such materials due to their renewability and intrinsic rigidity, but they have not been extensively studied. Herein, biomass-based polyureas were prepared by polymerizing dicarbamates derived from furfurylamine and isomannide. The dicarbamates were produced in multigram-scale quantities with high purity and yield. A series of polyureas with reasonably high molecular weights were subsequently prepared by condensing the dicarbamates with various diamines. 1H NMR and 13C NMR spectroscopy confirmed the structure of the targeted copolymers. Exploration of thermal behavior by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) revealed that the synthetic polyureas showed good thermal stability and glass-transition temperatures (Tg) ranging from 11 to 213 °C.